Real Outfit Roundup: 11 Winter Outfits to Inspire You
Welcome to the first outfit roundup of 2025! This is where I share outfits that I wore in real life along with links to shop the same or similar items. I also tell you where I wore it and my thoughts on how it all came together.
These outfits date back pretty far -- as in before Christmas break. That's because once I went on break, I kind of hibernated. Okay, so not really, but we did end up passing around some kind of viral cold so we didn't go on all that many outings this year.
All of these outfits were posted to my Like to Know It shop within a day or two of me wearing them, so if you're not following me there, you need to be! It's the best way to make sure you can get exact items before they sell out. You can also access all of that content via the Shop My Instagram tab at the top of this page or through my Instagram and Facebook pages.
Sizing info: I'm 5'2" and wear size 6 or s/m in clothes and size 7 in shoes.
I wore this the last week of school before Christmas break. I wanted to feel Christmasy but also professional. I love this skirt so much but have a hard time styling it. Until this blouse, I didn't have many tops that meshed well with the colors in the skirt's pattern.
The skirt is a pale gold base with red flowers on green vines, so it's perfect for the holiday season. I really love it with this green lace blouse. The bodice of blouse is lined but the sleeves are not, which makes it perfect for our typically not cold winters. I got this in a medium since it's a button-up, but beware -- it shrank a bit in the wash. I really only noticed it in the sleeves, though.
I decided to keep things feeling wintry with my tall brown boots, although we really were not cold this particular week at all. I love these boots, but I got them at the end of the season a couple of years ago and they discontinued them. Thankfully, I found a really similar pair for you!
This is also from the week before Christmas break, and yes, I am aware that it looks more like Thanksgiving than Christmas, but I ordered these pants for Thanksgiving and they had just come in, so I wanted to wear them. They are a lot more orange than I expected. I felt like I should be pairing them with camo and heading to a deer stand! So my goal with the rest of this outfit was to tone down the pants. I don't think it worked, though, and I wasn't really happy with this outfit.
I've really enjoyed this sweater vest this winter. You can't tell from this picture, but it's got a mock neck, which took a little getting used to for me since I don't particularly enjoy stuff on my neck/throat. Because it was very much not cold but not warm enough for sleeveless, I layered the vest over one of my long-sleeve layering tees (you know -- the ones from this post). I finished the outfit with my brown heeled Chelsea boots.
I think if my pants had been more of a burnt orange, like the picture on the product page, I would have liked this outfit much better. But alas, the pants just felt like a glowing beacon screaming look at me all day long. Don't get me wrong. Aside from the ridiculously bright color, these pants were nice quality. The wideness of the legs was just right and they were comfortable. I feel like I will probably get more use out of them in warmer months, though, when colors this bright feel more appropriate.
This is the last before-Christmas outfit. I wore this out shopping with my mom and daughter. It was colder but not frigid, and this outfit was perfect. Unfortunately, everything in this outfit is old. I've had these pants for more than five years, and the sweater is going on three or four. My boots are still available, though!
Welcome to January! This was what I wore for New Year's Day. We had lunch with my parents, went out to the barn to work with the pigs, and then had dinner with my in-laws. This is one of my oldest outfits. This exact colorway of the tunic sweater dress is no longer available, but the one I linked to is almost exact, just a bit brighter. I've got the black version of the one I linked to and it's good quality and one of my most-worn winter pieces.
These leggings are actually the only leggings I own. They are so soft and buttery feeling. They're comfortable all day long, and I don't have issues with bunching or sagging. I highly recommend!
This was last Saturday, January 4th...and I don't remember what we did if I'm being honest. I know the day before we were in Eufaula, but the only record I have from this day is making spaghetti and meatballs for dinner. That means we had to have gone to the grocery store, but that's literally all I remember.
My sweater is really old but one of my favorites ever from Old Navy. They have one that's pretty similar right now that I'm linking to for you. My pants -- yes, pants, not leggings -- are the Stevie skinnies that I've been wearing for years. These give you the illusion of leggings but they're so much better. They're really thick so no need to worry about unseemly lines and they've got a tailored seam going down the leg fronts to make them look polished.
Let's talk about my socks. I've had these sweater socks for years, and they're seriously one of the greatest things I have ever bought for myself. They are the perfect boot sock! I wear them all. the. time. in the winter.
This was my first day back to work, and as you can tell by my hair -- it was windy af. I've had this sweater for so long, y'all. It's one of my favorites, even if it's not exactly "trendy" anymore. I don't care. When you really love something, keep on wearing it! Anyway, it's no longer available but I found something similar, although I don't think the quality is the same.
My jeans are mid-rise bootcut, but I have to say that on me they feel almost low-rise compared to the other pair I have in a different wash. My boots are also really old. I got them from Target of all places, and they're really good quality considering the low price point. I got them back when boots with lots of buckles were trendy, and I wasn't sure if I would like them, and they became my favorite pair of flat boots. I linked to similar pair, although neither has near the number of buckles as mine.
This was day two back at work, still with no students and still cold. I really wanted to wear this short-sleeve sweater that reminds me of my recently-passed grandmother, but it needed a more substantial under-layer than the camisole I usually wear. I really like the juxtaposition of this brown long-sleeve tee. It feels unexpected but also kind of obvious.
My jeans are the same bootcut as with the previous outfit, but they fit differently. This pair is actually a little looser in the hips and an inch or two longer. Go figure.
This was the students' first day back from Christmas break. I went through so many outfit choices before landing on this one. It was really cold, so I wanted layers. Not pictured here is the purple-red long cardigan I wore over this all day at school.
These overalls have been a workhorse in my school wardrobe this year. They are so versatile and so comfy. They come in quite a few colors. I've got the black already and just ordered the green. I get these in a medium so they're extra roomy, but they do have adjustable straps.
My blouse, unfortunately, is no longer available. Old Navy usually comes out with updated patterns/colors for this style shirt, but I'm not seeing any on their site right now.
This was Thursday - day two of students' being back at school. It was still super cold, both outside and in the hallway, but the inside of my classroom was feeling a bit like a furnace. That meant I needed layers once again. Good thing this super adorable, 3D sweater vest arrived just in time!
I am in love with this sweater vest. The flowers really are 3D, which just gives it that much more personality. Obviously, I'll have to be really careful when I wash it. I had lots of ideas for how to layer it but decided to keep things classic this first go 'round with a white button-up over my black Stevie pants. I finished the look with my buckle boots.
This was our first Friday back at school and my favorite work outfit of the week. I styled everything around these jeans-that-don't-really-look-like-jeans. The legs have a jacquard pattern with the pockets being a solid dark navy blue. They're high-waisted and wide-legged and absolutely gorgeous. I'm wearing the large.
I decided that I wanted to go with a monochrome look, especially since this fair isle sweater was almost an exact match for the pattern on the jeans. I've had this sweater for a really long time, but fair isle is a classic style that you can find pretty much all the time. I linked to a couple of similar options for you.
That brings us to yesterday, which was a Saturday. Alexis had Odyssey team practice so I spent the morning working on my gifted endorsement homework in my classroom. I did go out to the barn around lunchtime to assist in getting the pigs weighed and then had lunch with my parents and the coworker who brought the scales. Afterwards, I picked up Alexis and headed back home where I spent the afternoon doing more homework before meeting Chris for dinner after he got off work.
Let's talk about these jeans! They're running neck and neck with the jeans in the previous outfit for favorite jeans purchase of the new year. They have got the prettiest blue-and-cream floral pattern on them. They're high waisted and wide legged and fit like a dream. They are not super thick and are pretty soft. I'm wearing the large.
My cardigan sweater is from two years ago, but I linked to the exact style at Old Navy and a similar, cheaper option that looks almost exactly the same.
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